Tris(furan-2-yl)phosphane → N-{[(5S)-3-(4-{5-[5-(Hydroxymethyl)-4,5-dihydroisoxazol-3-yl]thien-2-yl}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide

HRID 747245노트

반응식

HRID 747245 반응식
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([Sn](C)(C)C)=[CH:9][CH:8]=2)[CH2:5][C@H:4]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:3]1.Br[C:23]1[S:27][C:26]([C:28]2[CH2:32][CH:31]([CH2:33][OH:34])[O:30][N:29]=2)=[CH:25][CH:24]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[OH:34][CH2:33][CH:31]1[O:30][N:29]=[C:28]([C:26]2[S:27][C:23]([C:10]3[CH:11]=[CH:12][C:7]([N:6]4[CH2:5][C@H:4]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:3][C:2]4=[O:1])=[CH:8][CH:9]=3)=[CH:24][CH:25]=2)[CH2:32]1

참가 물질

5

반응물 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 14987823N-({(5S)-2-Oxo-3-[4-(trimethylstannyl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamideHCID 17954475[3-(5-Bromothien-2-yl)-4,5-dihydroisoxazol-5-yl]methanol

생성물 1

HCID 59749493N-{[(5S)-3-(4-{5-[5-(Hydroxymethyl)-4,5-dihydroisoxazol-3-yl]thien-2-yl}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide수율 42.1%

시약·촉매·용매 1

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)촉매

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온도
90 °C

실험 절차

N-({(5S)-2-Oxo-3-[4-(trimethylstannyl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamide (500 mg, 1.26 mM), [3-(5-bromothien-2-yl)-4,5-dihydroisoxazol-5-yl]methanol (330 mg, 1.26 mM), tris(dibenzylideneacetone)dipalladium (0)-chloroform adduct (130 mg, 0.126 mM) and tri-2-furylphosphine (58 mg, 0.252 mM) were placed in a flask. The solids were degassed and placed under nitrogen. Anhydrous dioxane (10 ml) was added and the suspension was heated at 90° C. for 16 hours. The reaction mixture was cooled and the solvent was evaporated. The residue was chromatographed on silica gel eluting with 5% methanol in dichloromethane to give the title compound (220 mg).

후처리

  1. customThe solids were degassed
  2. additionAnhydrous dioxane (10 ml) was added
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was evaporated
  5. customThe residue was chromatographed on silica gel eluting with 5% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-024e81dc726548a48e69f0ca86a3a623
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396847B2

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